Dimethylformamide → HCID 58709788, compound

HRID 2375901Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:10]2[S:14][CH:13]=[N:12][CH:11]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.Cl[C:16]1[N:17]=[CH:18][C:19]2[CH:24]=[C:23]([C:25]3[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH:30]=3)[NH:22][C:20]=2[N:21]=1.CN(C=O)C>C(O)CCC>[CH3:8][N:6]1[C:5](=[O:9])[C:4]([C:10]2[S:14][CH:13]=[N:12][CH:11]=2)=[CH:3][C:2]([NH:1][C:18]2[C:19]3[CH:24]=[C:23]([C:25]4[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH:30]=4)[NH:22][C:20]=3[N:21]=[CH:16][N:17]=2)=[CH:7]1

Participants

Conditions

Temperature: 120 °C

Procedure

5-Amino-1-methyl-3-thiazol-5-yl-1H-pyridin-2-one (99.0 mg, 0.478 mmol) was added to a solution of tert-butyl 4-(chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (133 mg, 0.398 mmol) in 1-butanol (2.0 L). The reaction was stirred at 120° C. for 15 h. DMF (1.5 mL) was added and the mixture was filtered. The filtrate was purified by HPLC to yield the title compound. 1H-NMR (CD3OD, 400 MHz): δ=1.50 (s, 9H), 2.57 (m, 2H), 3.67 (m, 2H), 3.73 (s, 3H), 4.13 (m, 2H), 6.30 (s, br, 1H), 6.62 (s, 1H), 8.21 (s, 1H), 8.33 (d, J=2.4 Hz, 1H), 8.34 (d, J=2.4 Hz, 1H), 8.47 (s, 1H), 8.99 (s, 1H). MS (ES+): m/z 506.08 [MH+]. HPLC: tR=2.62 min (ZQ2000, polar—5 min).

Workup

filtrationthe mixture was filtered
customThe filtrate was purified by HPLC

Sources & evidence

ORD record: ord-70e339ff883f4f11b6a6756669654e46
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465726B2

Reaction notes

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